N-(2-hydroxyethyl)-N-methylmorpholinium bromide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: N-(2-hydroxyethyl)-N-methylmorpholinium bromide
• 英文别名: N-(2-hydroxyethyl)-N-methylmorpholin-4-ium bromide；N-methyl-N-(2-hydroxyethyl)morpholinium bromide；N-(2-hydroxyethyl)-N-methyl-morpholinium bromide；2-(4-methylmorpholin-4-ium-4-yl)ethanol;bromide
• 化学式: Br*C₇H₁₆NO₂
• 分子量: 226.114
• InChiKey: YDOMEHLVYWIFAL-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -3.54
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(2-hydroxyethyl)-N-methylmorpholinium bromide 在 sodium azide 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以97%的产率得到hydroxyethyl methyl morpholinium azide
  参考文献：
  名称：

  羟乙基甲基吗啉叠氮化物（HEM Morph）N 3的合成：一种高效的基于新任务的叠氮化物型离子液体，并且可作为叠氮化物的来源和介质，用于合成某些新型芳香族O-肟醚-1,2,3 -三唑共轭物作为潜在的抗组胺药

  摘要：

  已经描述了作为新的基于叠氮化物的离子液体（ABIL）的羟乙基甲基吗啉叠氮化物（HEM Morph）N 3的合成，表征和应用。（HEM Morph）N 3用作叠氮化物的来源和O-炔丙基肟醚与烷基溴之间的三组分“点击” Huisgen环加成反应的反应介质，从而获得新型芳族O-肟醚-1,2,3-三唑偶联物作为潜在的抗组胺药，收率很高。研究了温度，IL量，叠氮化物型离子液体的类型及其可重复使用性等参数的影响。（HEM Morph）N 3 已被证明是一种高效，热稳定，廉价且可回收的基于叠氮化物的离子液体，可以轻松合成并用作“ Click” Huisgen环加成反应的叠氮化物来源和反应介质。

  DOI：

  10.1016/j.molliq.2019.112245
• 作为产物：
  描述：

  N-甲基吗啉 、 2-溴乙醇 以 乙腈 为溶剂， 反应 48.0h， 以77%的产率得到N-(2-hydroxyethyl)-N-methylmorpholinium bromide
  参考文献：
  名称：

  Fabrication of Metal Nanoparticles Using Hydroxylated Ionic Liquids

  摘要：

  在不添加任何添加剂的情况下，通过羟基化离子液体在水相中的自调节还原成功合成了金属纳米颗粒。描述了使用 N-(2-羟乙基)-N-甲基吗啉四氟硼酸盐水相合成金和钯纳米颗粒的新方法。采用透射电子显微镜来表征金属纳米颗粒。金和钯纳米颗粒的平均尺寸分​​别为 4.3 nm 和 3.2 nm。羟基化离子液体既充当还原剂又充当保护剂，显着简化了纳米颗粒的制备。产生的颗粒具有高度结晶结构，具有面心立方（fcc）晶格。最后，我们的初步结果表明不同的羟基化离子液体也可用于制备各种金属纳米粒子。

  DOI：

  10.1166/jnn.2011.3177

文献信息

• The influence of bromide-based ionic liquids on solubility of {LiBr (1) + water (2)} system. Experimental (solid + liquid) phase equilibrium data. Part 2
  作者：Marta Królikowska、Maciej Zawadzki、Michał Skonieczny

  DOI：10.1016/j.molliq.2018.06.006

  日期：2018.9

  (3)} ternary systems, with fixed IL to LiBr mass fraction w = 0.3 for all ILs and w = 0.1 and 0.2 for ammonium-based ILs and [MOR1,3SO3] have been performed by dynamic method. For all of the tested systems the transition point between lithium bromide dihydrate and monohydrate form was observed. Significant solubility enhancement of lithium bromide in water was obtained by adding ionic liquid, or zwitterionic

  这项工作的主要目的是研究离子液体（ILs）或两性离子化合物（ZI）作为LiBr（1）+ water（2）}系统的抗结晶添加剂，通常在吸收式制冷技术中用作工作对。在这项研究中，溴化锂在水中的溶解度已在较宽的温度和组成范围内测定，并与文献数据进行了比较。使用van't Hoff曲线计算二水合锂和一水合锂形式之间的转变温度和焓。这项工作的主要目的是确定和讨论在存在IL或ZI作为添加剂的情况下溴化锂在水中的溶解度。溶解度测量是使用动态方法在（230至370）K的温度范围内进行的。在这项工作中，新的介电常数为：N-甲基-N-（2-羟乙基）吗啉溴化物，[MOR 1,2OH ] [Br]，N-（2-乙酰氧基）乙基-N-甲基-吗啉溴化物，[MOR 1,2（OOC）1 ] [ Br]，N-甲基-N-（2-乙氧基-2-氧乙基）-吗啉溴化物，[MOR 1,1（COO）2 ] [Br]，1-甲基-3-（2-羟乙基）咪唑鎓溴化物，
• Antileishmanial Ring-Substituted Ether Phospholipids
  作者：Nikos Avlonitis、Eleni Lekka、Anastasia Detsi、Maria Koufaki、Theodora Calogeropoulou、Efi Scoulica、Eleni Siapi、Ioanna Kyrikou、Thomas Mavromoustakos、Andrew Tsotinis、Simona Golic Grdadolnik、Alexandros Makriyannis

  DOI：10.1021/jm020972c

  日期：2003.2.1

  Three series of ring-substituted ether phospholipids were synthesized carrying N,N,N-trimethylammonium, N-methylpiperidino, or N-methylmorpholino headgroups. The first series is substituted by 2-cyclohexyloxyethyl or 2-(4-alkylidenecyclohexyloxy)ethyl groups, the second series by cyclohexylidenealkyl or adamantylidenealkyl moieties, and the third series by 2-aryloxyethyl or 6-aryloxyhexyl groups in the alkyl portion of the molecule. The antileishmanial activity of the new compounds was evaluated in vitro against the promastigote forms of L. donovani and L. infantum using an MTT (3-(4,5-dimethylthiazol-2yl)-2,5-diphenyltetrazolium bromide)-based microassay as a marker of cell viability. Analogues 12, 15, 24, 30, 32, 41, 43, and 45 were more potent than the control compound miltefosine (hexadecylphosphocholine) against both L. donovani and L. infantum while, derivatives 13 and 42 were equipotent to miltefosine. Analogues 16, 17, 19, 20 were more potent than miltefosine against L. infantum and compounds 27, 31, 44 were more active than miltefosine against L. donovani. Differential scanning calorimetry (DSC) was used to probe the role of individual ether phospholipids on the physicochemical properties of model membranes. The DSC scans showed that the active compounds have a more profound effect on the thermotropic properties of model membrane bilayers than the less active ones.
• Design and Synthesis of Potent Antileishmanial Cycloalkylidene-Substituted Ether Phospholipid Derivatives
  作者：Theodora Calogeropoulou、Panagiotis Angelou、Anastasia Detsi、Irene Fragiadaki、Effie Scoulica

  DOI：10.1021/jm701166b

  日期：2008.2.1

  Two series of novel ether phospholipids (EPs) have been synthesized. The first includes cyclodecylideneor cyclopentadecylidene-substituted EPs carrying N,N,N-trimethylammonium or N-methylpiperidino or N-methylmorpholino head groups. The second series encompasses more rigid head groups in combination with cycloalkylidene moieties in the lipid portion. In addition, hydrogenated derivatives were obtained. All the new analogues, except 33, were 1.5- to 62-fold more potent than miltefosine against the intracellular L. infantum, and the most active ones were also less cytotoxic against the human monocytic cell line THP1 and less hemolytic than miltefosine. The analogues that combine high potency with low cytotoxicity and hemolytic activity were 19, 37, 2123, 38, 39, and 40. Cyclopentadecylpentylphosphocholine (38) possesses an IC50 of 0.7 mu M against L. infantum amastigotes and is the least cytotoxic analogue, since it does not present toxicity against THP1 macrophages, even at a concentration that is 800-fold the antiparasitic IC50 value, and does not present significant hemolytic activity.
• Alkyl and Alkoxyethyl Antineoplastic Phospholipids
  作者：Maria Koufaki、Vanessa Polychroniou、Theodora Calogeropoulou、Andrew Tsotinis、Markus Drees、Heiner H. Fiebig、Sophie LeClerc、Hans R. Hendriks、Alexandros Makriyannis

  DOI：10.1021/jm9509152

  日期：1996.1.1

  Two series of phosphodiester ether lipid analogs with (N-methylmorpholino)ethyl or (N-methylpiperidino)ethyl polar head groups and long aliphatic or alkoxyethyl chains in the nonpolar portion of the molecule were synthesized as potential antineoplastic agents. The cytotoxic activity of these compounds (9-19) was evaluated in vitro against a panel of six human tumor xenografts and in two biochemical, mechanism-based screens (cdc2 kinase and cdc25 phosphatase). Analogs 13, 14, 17, and 19 showed activity in the in vitro tests. Specifically, 14 and 17 were more active than the reference compound hexadecylphosphocholine (Miltefosine, He-PC) while 13 and 19 possessed activity similar to that of the control. Of the analogs tested the one with the highest potency and least toxicity (17) has an N-methylpiperidino head group and a C-16 alkyl chain. In the mechanism-based tests 11 showed weak inhibitory activity in the cdc25 phosphatase screen.
• EP1461041A4
  申请人：——

  公开号：EP1461041A4

  公开（公告）日：2006-03-29